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How often should I boil out my deep fryer?

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Opinions differ, but generally you should schedule a boil out every 3 or so months, and don't be afraid to perform a boil out sooner if the residue accumulation demands it. Thankfully, performing a boil out isn't all that complicated. Simply drain the fryer oil, fill the vat with warm water and cleaning solution, and turn the fryer on so that it the water is simmering. While the water is simmering, scrub the vat with a brush (wear protective gloves!). After you have cleaned the vat to your satisfaction, drain the water and cleaning solution, rinse the vat, and refill the fryer oil.

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It entirely depends upon how much you are using your fryers. If you are selling fries almost every or every other order and it's a busy restaurant, then you can even do a boil out twice a week. Once at the beginning of the week after a busy weekend rush and one right before the weekend rush.
While oil is expensive, I have found that product quality control is vastly more important. You can use the a taste test to really tell. The other indicators are:
that the oil will be dark and you won't be able to see the heating unit
burning smell
smoke rising off the heating element.
On much equipment cleaning solution is not preferred as long as you have a good scratch pad, the steam should be sufficient to clean out the unit. Make sure not to burn yourself.